Synthetic method of pyrrole fused-ring 3-indolone type compounds

A synthesis method and compound technology, applied in organic chemistry and other fields, can solve problems such as poor atom economy, high potential danger, and difficulty in raw material construction, and achieve the effect of short route, high application value, and promotion of deep-level expansion

Inactive Publication Date: 2015-04-08
EAST CHINA NORMAL UNIV +1
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Problems solved by technology

In the above reactions, there are difficulties in the construction of raw materials, many reaction steps, and poor atom economy; in addition, the potentially dangerous carbon monoxide gas is used in route a, and 2,5-dimethyl, which is less stable, is used in route b. Oxyfuran, route c adopts the method of Friedel-Crafts reaction, the post-treatment is more cumbersome, and may even affect the yield

Method used

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  • Synthetic method of pyrrole fused-ring 3-indolone type compounds
  • Synthetic method of pyrrole fused-ring 3-indolone type compounds
  • Synthetic method of pyrrole fused-ring 3-indolone type compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] Under the protection of an inert gas, the fused ring isatin compound 1 (0.20mmol) and the alkyne compound 2a (1.00mmol) were dissolved in acetonitrile / 1,4-dioxane (2.00mL) (v / v=1:1 ), add palladium acetate (0.02mmol), silver acetate (0.40mmol), the reaction system was stirred for 12 hours at 100°C, and detected by TLC. After drying, the solvent was removed by spinning to obtain a crude product, and the product 3a was obtained by flash column chromatography with a yield of 63% (recovered yield 85%). 1 H NMR (500MHz, CDCl 3 ): δ=7.76(t, J=8.0Hz, 2H), 7.63(d, J=8.0Hz, 1H), 7.56-7.54(m, 2H), 7.46(t, J=8.5Hz, 1H), 7.38 -7.30(m, 8H), 7.20-7.17(m, 3H), 7.02(dd, J=7.0, 2.0Hz, 2H), 6.81-6.77(t, J=8.0Hz,, 1H), 6.67(d, J = 8.5Hz, 1H); 13 C NMR (125MHz, CDCl 3 ):δ=179.85,144.00,138.77,136.91,134.11,132.69,132.23,131.73,131.56,131.28,130.24,129.92,129.72,129.49,129.29,128.76,128.49,128.31,128.10,127.22,127.08,126.20,125.58, 121.40, 120.06; calculated HRMS (ESI) C 3...

Embodiment 2

[0029]

[0030] The operation steps are the same as in Example 1, and the yield is 62% (the recovered yield is 91%). 1 H NMR (500MHz, CDCl 3 ): δ=7.76-7.72(m, 2H), 7.62(d, J=8.5Hz, 1H), 7.54(dd, J=7.0, 2.0Hz, 2H), 7.26(d, J=1.5Hz, 1H) , 7.25(d, J=1.5Hz, 2H), 6.93(d d, J=7.0, 2.0Hz, 2H), 6.89(t, J=2.0Hz, 2H), 6.84(dd, J=7.0, 2.5Hz, 2H), 6.77(d, J=8.5Hz, 1H), 6.76-6.74(m, 1H), 3.85(s, 3H), 3.81(s, 3H), 3.78(s, 3H); 13 C NMR (125MHz, CDCl 3 ):δ=179.59,160.77,160.07,158.79,143.87,138.71,137.21,133.01,132.63,132.42,131.70,129.38,129.28,129.02,127.96,126.76,126.72,126.13,125.75,125.07,124.34,121.47,120.11, 114.97, 114.06, 113.77, 55.88, 55.67, 55.59; HRMS (ESI) calculated value C 36 h 27 NNaO 4 [M+Na] + 560.1832, actual value 560.1837..

Embodiment 3

[0032]

[0033] The operation steps are the same as in Example 1, and the productive rate is 52% (the productive rate is 79% after raw material recovery). 1 H NMR (500MHz, CDCl 3 ): δ=7.78(d, J=8.5Hz, 1H), 7.73(d, J=8.0Hz, 1H), 7.67(d, J=8.0Hz, 1H), 7.45-7.42(m, 2H), 7.39 -7.36(m, 3H), 7.30-7.26(m, 4H), 7.22-7.20(m, 2H), 6.93-6.89(m, 3H), 6.72(d, J=8.5Hz, 1H); 13 C NMR (125MHz, CDCl 3 ):δ=179.78,143.82,138.92,136.33,135.39,134.87,133.70,132.98,132.44,132.11,131.47,130.73,130.59,130.01,129.64,129.57,129.19,128.82,128.66,128.61,128.47,127.57,126.47, 125.20, 121.25, 120.15; HRMS (ESI) calculated value C 33 h 19 Cl 3 NNaO[M+Na] + 572.0346, actual value 572.0353..

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Abstract

The invention discloses a synthetic method of pyrrole fused-ring 3-indolone type compounds. The synthetic method comprises the following step: reacting fused-ring isatin type compounds and double-substituted acetylene type compounds as raw materials in a reaction solvent under the atmosphere of nitrogen and under the action of a palladium metal catalysis and oxidation agent to obtain the pyrrole fused-ring 3-indolone type compounds. According to the synthetic method of the pyrrole fused-ring 3-indolone type compounds, disclosed by the invention, the raw materials are simple and easy to be obtained, the economy of atoms is high, the path of synthesis method is simple and convenient, and the efficiency is excellent.

Description

technical field [0001] The invention specifically relates to a method for synthesizing pyrrole-condensed ring 3-indolinone compounds, which belongs to the technical field of organic compound technology application. Background technique [0002] In recent years, chemists have been looking for greener organic synthesis methods. C-H bond activation has attracted the attention of many chemists due to its excellent characteristics in environmental friendliness and sustainability. Among them, through multi-site activation, one-time It is the common goal of chemists to construct a complex molecular skeleton. The present invention realizes Pd-catalyzed C-H / N-H bond breakage and completes the oxidative ring addition of alkyne compounds to construct nitrogen-containing heterocyclic compounds. This method is atom-economical High performance and short steps. [0003] Pyrrole indole ring skeletons are widely found in a series of natural products and are an indispensable type of molecula...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
Inventor 姜雪峰汪舰李一鸣黄家尧李文军
Owner EAST CHINA NORMAL UNIV
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